20 Cute Dressy Winter Outfits With Boots, Bows and Pretty Layers

Looking for cute dressy winter outfits with a little something extra? Think burgundy skirts, cream dresses and a red coat with a bow at the neckline.

These looks include dressed-up dinner ideas plus a few more casual combinations you can change up with your accessories.

You can keep things simple or go all out with sparkle. Some looks are better starting points for indoor plans, so add suitable outerwear and leg coverage for the weather.

There’s plenty here to save for your next outfit!

Dressy winter outfit ideas to save

cream mini and long scarf

We’re starting off strong with this pretty cream dress and matching tall boots. I love the long fringed scarf draped over the fitted mini.

Wrap your scarf loosely around your neck and let the ends hang down the front to follow this look. You don’t need lots of accessories here.

shaggy coat and black mini

How cute is this coat? The beige and brown stripes look so good over the simple black mini dress and sheer black tights.

The small black shoulder bag keeps the rest understated.

If you want your coat to be the main detail, try an all-black outfit underneath like this one.

white scarf blouse and burgundy

This blouse may just be one of my favorites here. I love the long white neck tie against the burgundy mini skirt.

The white shoulder bag is such a pretty match.

Tuck your blouse into the skirt and leave the tie hanging down one side to recreate the combination.

checked blazer and tall boots

Don’t want to wear a dress and want something super simple? This checked blazer over a black top and fitted black pants is for you.

The tall black boots and little top-handle bag dress it up without adding another color.

burgundy midi and black

I am obsessed with this burgundy skirt. The glossy finish looks gorgeous beside the plain black turtleneck, especially with that slim belt at the waist.

Try black pointed boots underneath the midi hem to keep the same combination. I’d leave the accessories just as simple.

cream layers and blue jeans

If you love jeans but want to dress them up a little, start here. The long cream coat, high-neck sweater and fringed scarf look so pretty together.

The brown bag matches the belt and pointed boots. Keep those darker accessories if you’re putting together your own version.

brown plaid and white leg warmers

How adorable is this plaid skirt? I love it with the loose brown sweater and little brown shoulder bag.

The white leg warmers over black tights give this outfit a more playful finish. Try them with dark loafers like the ones here if you want something different from tall boots.

burgundy from coat to boots

If you are looking for a head-to-toe color idea, then this one is for you. There’s burgundy on the long coat, high-neck top, glossy mini skirt and pointed boots.

I especially love the matching curved bag. You can mix slightly different shades rather than trying to match every piece exactly.

taupe top and brown midi

Don’t want to go overboard with accessories? No problem!

Try this taupe ribbed top tucked into a dark brown midi skirt. The little bows on the pointed shoes are my favorite detail.

cream coat and dotted headband

This is such a pretty way to dress up a coat. I love the little white beads across the black headband, especially with the black gloves and structured bag.

Start with a cream coat over a black high-neck top. Then add a small pendant necklace like the one here.

big bow and pleated trim

The bow fans are going to love this! The oversized black neck bow sits above a row of bright round buttons on this black-and-white mini dress.

The pleated cuffs and matching hem are just as cute. I’d keep the small white bag to bring out the lighter details in the dress.

gray trousers and white collar

If you’re looking for something a little more tailored, go with these gray pleated trousers and a dark sweater. A white shirt collar peeks out at the neckline.

Add a long dark coat and a narrow belt with a gold-tone buckle to follow the outfit. The pointed black shoes finish it off.

gray set and burgundy bow

How cute is this oversized hair bow? The long burgundy tails look so pretty against the gray sweater and pleated mini skirt.

Read also: 20 Korean Date Night Outfits With Pretty Skirts, Bows and Simple Layers

The matching burgundy bag makes this a lovely idea to save when you’re searching for cute dressed up outfits winter inspiration. Try a bow and bag in the same color with a gray set you already own.

Read also: 20 Outfit Ideas for a Dinner Party at Home

green dress and floral tights

I am obsessed with this deep green dress. It’s so pretty with the curved neckline and gathered detail at the waist, plus those floral tights are adorable.

Keep the black heels if you’re wearing this for an indoor party. The tights already add plenty of pattern.

gray sweater and white accents

This is another cute mini skirt outfit, but the little white details make it different. I love how the high neckline matches the socks peeking above the black boots.

Layer a loose gray sweater over a white high-neck top, then pair it with a black mini and sheer black tights.

cream sweater and plaid pleats

Love a plaid mini but want a more casual version? This cream cable-pattern sweater and brown checked skirt make a cute starting point.

The short tan boots and scrunched white socks keep it relaxed. For a dressier variation, I’d switch those for tall brown boots and keep the cream-and-brown tote.

one-shoulder sparkle and dark jeans

Who says you have to wear a skirt to dress up? This sparkling black top looks gorgeous with dark wide-leg jeans.

I especially love the one-shoulder neckline and long flared sleeve.

Add pointed black shoes and a small black bag to keep the rest simple.

cream cape and tied waist

This cream cape jacket may just be my favorite outerwear idea here. The high buttoned collar and big waist tie are so pretty over the fitted black outfit.

Keep your black sleeves showing beneath the cape. Tall pointed boots and a small brown bag complete the combination.

Read also: 20 Classy Winter Lunch Outfit Ideas With Coats, Skirts and Simple Layers

white mini and burgundy boots

I love this white ribbed dress with its flared cuffs. The dark burgundy boots and matching shoulder bag are just too pretty together.

If you want a change from an all-cream outfit, try adding these darker accessories instead.

red bow coat and black boots

Last but definitely not least, we have this gorgeous red coat. I am obsessed with the bow at the neckline!

The matching red buttons and turned-back cuffs are such lovely details.

Pair yours with black tights, tall black boots and a small black bag to follow this look.